Genesis 49:12

How beautiful are the eyes of the king Meshiha, as the pure wine! He cannot look upon what is unclean, nor on the shedding of the blood of the innocent; and his teeth, purer than milk, cannot eat that which is stolen or torn; and therefore his mountains are red with wine, and his hills white with corn, and with the cotes of flocks.

HIS EYES ARE ‘CHACHLILI’ (FROM WINE). The Commentators say that the word chachlili denotes redness, and it means that his eyes will become red from drinking much wine. Of similar meaning is the verse, Who hath ‘chachliluth’ (redness) of the eyes?
Now it appears to me that this is a case of a word whose letters are transposed,, it should be understood as if it were written: kaf, cheth, lamed, suggesting the act of painting, as will be explained further. it being derived from the expression, Thou didst paint (‘kachalt’) thine eyes. The lamed is doubled — [chachlili] — as is customary in many places, and it denotes the process of painting eyes which is known and frequently mentioned in the words of our Rabbis. In Arabic also its name is “al kachul.” The verse is thus stating that Judah’s eyes are colored with wine for just as others paint them with puch (eye-paint), which is the Arabic “al kachul,” so does he paint them with wine, and just as others whiten their teeth with ointments, so does he whiten them with milk, the comparison indicating the abundance of wine and milk in Judah’s land, just as Onkelos mentioned. Similar in meaning is the verse, Who hath ‘chachliluth’ of eyes, [the letters in the word chachliluth are to be transposed to read] kachliluth (paint), with the verse stating that the drunkard has his eyes painted by wine and he cannot hide his drunken state. It is possible that the verse is stating, “Who has coloring of eyes?” meaning “who needs to paint his eyes always? They that tarry long at the wine, since the wine dims their eyes, causing them to tear, and be consumed away in their sockets, thus making it necessary for him to have his eyes constantly painted.” Scripture, in the book of Proverbs, is thus speaking of the disgrace of wine and the external evils of contentions and wounds which befall he who drinks it in abundance, while in his house there will always be the cry of “Woe” and “Alas.” It then also mentions this specific harm which affects his body, namely, the dimming of his vision, and many other sicknesses. This is a correct interpretation and elucidation of the subject.

חכלילי, the redness of eyes is called thus.

ולבן-שנים, the result of drinking milk produces this whiteness of the teeth. We find a parallel expression in Song of Songs 5,1 שתיתי ייני עם חלבי, “I have drunk my wine with my milk.” Isaiah 55,1 describes a similar theme,בלא כסף ובלא מחיר יין וחלב, “(come buy). without money or any cost, wine and milk. “The word “ul-ven,” must be understood as if it had the vowels making it “ulavan.” When it is in a possessive mode, the grammar is quite in order so that it is ulven. In a similar possessive mode in Deuteronomy 32,14 we find “vachalev tzon,” describing “the chalav of sheep.”

חכלילי עינים מיין, the fifth of the identifying marks of the Messiah will be the onset of an unusually long period of economic progress, plentiful harvests, etc. This has also been predicted in Psalms 72,16 “let abundant grain be in the land to the tops of the mountains, let his crops thrive like the forest of Lebanon.” Our sages have paraphrased this in Shabbat 30 when they described the affluence in messianic days by crediting the soil of Israel with producing ready to eat rolls and garments made of the finest wool.

Yaakov adds something else which is an exaggeration when he says: חכלילי עינים סותה, not only Yehudah’s clothing would be red but even his face and eyes. The word עינים describes the exterior appearance, as in Proverbs 23,29 למי חכלילות עינים? “Who suffers from redness of his eyes? The word עין, עינים, to describe an exterior appearance is also used to describe the manna in Numbers 11,7.

ולבן שנים מחלב. Due to drinking a lot of milk his teeth are white. Some commentators understand the word שנים in our verse as describing the teeth-like points of the rocks being white from the drippings of excess milk by the sheep and goats. Accordingly, even these so-called teeth have to be explained allegorically, as a reference to the Messiah. [I believe that all the commentators who chose the path of interpreting Yaakov’s words allegorically, simply could not credit that he would waste his last few minutes on earth with describing mundane matters as being the essence of what he had to communicate to his children at that time, even if these words were garbed in poetic language. The sages were convinced that behind this lovely prose there must be hidden far more profound spiritual messages. Ed.]

To continue with the “Messianic” interpretation. אסרי לגפן עירה, the word הגפן is a metaphor for the concept of the Jewish nation, כנסת ישראל, an expression used in the same sense in Psalms 80,9 גפן ממצרים תסיע, “You transplanted a vine (the people of Israel) from Egypt.” Just as the word גפן is used as a metaphor for the Jewish people in Psalms, so the word שרקה is used in a similar sense in Jeremiah 2,21, ואנכי נטעתיך שורק כלו זרע אמת, “whereas I had planted you as a vine, all with the choicest seed.” The prophet, of course, compares the Jewish people to a vine, normally yielding excellent grapes, but somehow having become corrupted. When such vines are at their best, the grapes they produce do not even have kernels, (i.e. seedless grapes)

חכלילי עינים מיין, ‘he will be red-eyed from wine;” having drunk a great deal of wine, the colour of his face will reflect this. (Compare Samuel I 16,12). [The comment is complimentary in nature. Ed.]

ולבן שנים מחלב, “and his teeth whiter than milk.” The phrase is a metaphor for wishing good health, even one’s teeth being free from white milk. We find a similar metaphor in Lamentations 4,7: צחו מחלב, “whiter than milk;”